WO2017134468A1 - Succinate salt of cytisine and use thereof - Google Patents
Succinate salt of cytisine and use thereof Download PDFInfo
- Publication number
- WO2017134468A1 WO2017134468A1 PCT/GB2017/050294 GB2017050294W WO2017134468A1 WO 2017134468 A1 WO2017134468 A1 WO 2017134468A1 GB 2017050294 W GB2017050294 W GB 2017050294W WO 2017134468 A1 WO2017134468 A1 WO 2017134468A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- cytisine
- salt
- succinate
- lactose
- pharmaceutical composition
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/36—Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
Definitions
- the present invention relates to a novel salt of cytisine.
- the invention also relates to pharmaceutical compositions comprising a novel cytisine salt.
- Cytisine is a pyridine-like alkaloid known to be a potent nicotinic acetylcholine receptor agonist. Pharmacologically, cytisine exhibits a high degree of similarity to nicotine. Numerous studies have indicated that cytisine is useful in the treatment of nicotine addiction.
- a pharmaceutical smoking cessation product containing cytisine has been commercialised for several years under the brand name Tabex®.
- the Tabex® product is marketed in the form of an orally administered tablet comprising 1 .5mg of cytisine free base. While the product has been found to be efficacious and has been commercially successful, the approved shelf life of the product is two years.
- lactose may destabilise tablets comprising cytisine due to the presence of a carboxyl group in the lactose molecule, which is not completely inert chemically and may lead to a Maillard reaction. Accordingly, there is a need in the art for a form of cytisine which inherently is more compatible with conventional excipients such as lactose.
- the present inventors have surprisingly and unexpectedly identified a novel salt of cytisine which displays improved excipient compatibility and can be formulated with lactose as an excipient.
- a succinate salt of cytisine in embodiments of the present invention, may be present in the form of a solvate or a hydrate.
- the salt is preferably cytisine hydrogen succinate.
- a pharmaceutical composition comprising the succinate salt of cytisine and a pharmaceutically acceptable carrier.
- the pharmaceutically acceptable carrier is lactose.
- the lactose may be lactose monohydrate or anhydrous lactose.
- the compositions disclosed herein may be suitable for administration by any route known in the art.
- Pharmaceutical formulations encompassed within this aspect of the invention include those suitable for oral, nasal or topical administration.
- the composition may be formulated in a solid form such as a tablet or a capsule.
- excipients that may be employed in the compositions of the present invention, these include fillers, disintegrants, preserving agents, lubricants (e.g. magnesium stearate) and / or wetting agents.
- fillers include lactose (either anhydrous or monohydrate), cellulose, starch (e.g. corn and / or wheat starch), calcium phosphates, mannitol and others known in the art.
- Preserving agents prevent bacterial or fungal contamination of the formulation and may include various antibacterial and antifungal agents such as parabens, chlorobutanol, phenol or sorbic acid.
- the pharmaceutical composition may be coated according to any method known in the art, for example using collidone or shellac, gum arabic, talc, titanium dioxide or sugar.
- the pharmaceutical compositions of the invention may further comprise sweetening, flavouring or colouring agents.
- these may be prepared by any suitable method.
- such capsules may be prepared by mixing the salts with inert carriers such as lactose or sorbitol and packing them into gelatine capsules.
- the pharmaceutical composition will be provided as a unit dosage form (e.g. a tablet, capsule).
- the amount of cytisine succinate salt in the composition may range from about 0.5mg or about 1 .0mg to 2.0mg, 3.0mg, 5.0mg or about 10mg.
- the pharmaceutical compositions of the present invention may have a shelf life greater than 2 years when stored at 25°C and at a relative humidity of 60% ⁇ 5%.
- Figure 1 shows HPLC chromatograms of cytisine at (a) 310nm and (b) 203nm.
- Figure 2 shows HPLC chromatograms of succinic acid at (a) 310nm and (b) 203nm.
- Figure 3 shows HPLC chromatograms of cytisine succinate at (a) 310nm and (b) 203nm.
- Figure 4 shows the HR MS spectra of cytisine succinate: (a) ESI+ and (b) ESI-
- Figure 5 shows the MS-MS spectra of cytisine succinate: (a) ESI+ and (b) ESI-
- Figure 6 shows the IR spectra of cytisine succinate: (a) FTIR and (b) FTIR (ATR)
- Figure 7 shows the peak purity determinations using a DAD detector for cytisine hydrogensuccinate (a) succinic acid and (b) cytisine).
- the obtained salt was also subjected to high resolution mass spectrum analysis (Figure 4), tandem mass spectroscopy (Figure 5), IR spectroscopy ( Figure 6) and UV / VIS analysis ( Figure 7) was performed.
- Example 3 Samples of cytisine succinate salt obtained from Example 1 were formulated in standard formulations to investigate their stability, and the compatibility of the API with the excipients used. Preliminary analysis of these formulations indicates that the formulations comprising succinate salt are significantly more stable than those comprising cytisine free base.
- Example 3 Salt Screen
- suitable salts could not be formed with the common acid salt formers acetic acid, ascorbic acid or benzoic acid.
- the succinate salt was readily formed, exhibiting advantageous properties.
- Cytisine 0.9541 g, was dissolved in water, 1 ml, and afforded a yellow solution.
- Succinic acid 0.5919g, l equiv, was charged as a solid to the cytisine solution and dissolved slowly with agitation.
- Acetone 10ml, was charged and afforded a partitioned mixture of cytisine/succinic acid/water solution, lower, and acetone, upper. Trituration of a portion of cytisine/succinic acid/water solution with acetone, 10ml, converted the viscous mixture to a white solid which settled.
- the white suspension was charged to the remainder of the cytisine/succinic acid/water solution/acetone mixture with a rinse of acetone, 10ml, and agitation continued. This converted the viscous cytisine/succinic acid/water mixture to a white suspension which settled when agitation was stopped.
- the solid was isolated by filtration and dried in vacuo at 50 °C for ca 16 hours. The recovered solid was confirmed as being cytisine succinate by 1 H NMR analysis. Recovery: 1 .5463g, 80.76% based upon a salt stoichiometry of cytisine to succinic acid of 1 :1
- the chemical purity of a cytisine/lactose mixture was 99.83 area% and a cytisine succinate/lactose mixture was 99.68 area% at the start of the of the stability study.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Addiction (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PL17704814.7T PL3411029T3 (pl) | 2016-02-05 | 2017-02-06 | Sól bursztynianowa cytyzyny i jej zastosowanie |
EP17704814.7A EP3411029B1 (en) | 2016-02-05 | 2017-02-06 | Succinate salt of cytisine and use thereof |
CN201780009979.0A CN108883101A (zh) | 2016-02-05 | 2017-02-06 | 野靛碱的琥珀酸盐及其用途 |
DK17704814.7T DK3411029T3 (da) | 2016-02-05 | 2017-02-06 | Succinatsalt af cytisin og anvendelse deraf |
AU2017215300A AU2017215300B2 (en) | 2016-02-05 | 2017-02-06 | Succinate salt of cytisine and use thereof |
KR1020187025475A KR20180121900A (ko) | 2016-02-05 | 2017-02-06 | 시티신의 숙시네이트 염 및 그의 용도 |
MX2018009364A MX2018009364A (es) | 2016-02-05 | 2017-02-06 | Sal de succinato de citisina y uso de la misma. |
US16/075,902 US10300050B2 (en) | 2016-02-05 | 2017-02-06 | Succinate salt of cytisine and use thereof |
ES17704814T ES2963451T3 (es) | 2016-02-05 | 2017-02-06 | Sal succinato de citisina y uso de este |
EP23197173.0A EP4265298A3 (en) | 2016-02-05 | 2017-02-06 | Salt |
CA3013454A CA3013454C (en) | 2016-02-05 | 2017-02-06 | Succinate salt of cytisine and use thereof |
KR1020247009722A KR20240042257A (ko) | 2016-02-05 | 2017-02-06 | 시티신의 숙시네이트 염 및 그의 용도 |
JP2018541196A JP6820344B2 (ja) | 2016-02-05 | 2017-02-06 | シチシンのコハク酸塩およびその使用 |
SI201731450T SI3411029T1 (sl) | 2016-02-05 | 2017-02-06 | Sukcinatna sol citizina in njena uporaba |
ZA2018/05296A ZA201805296B (en) | 2016-02-05 | 2018-08-10 | Succinate salt of cytisine and use thereof |
AU2022203808A AU2022203808B2 (en) | 2016-02-05 | 2022-06-02 | Succinate salt of cytisine and use thereof |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1602145.3 | 2016-02-05 | ||
GBGB1602145.3A GB201602145D0 (en) | 2016-02-05 | 2016-02-05 | Salt |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2017134468A1 true WO2017134468A1 (en) | 2017-08-10 |
Family
ID=55641904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2017/050294 WO2017134468A1 (en) | 2016-02-05 | 2017-02-06 | Succinate salt of cytisine and use thereof |
Country Status (16)
Country | Link |
---|---|
US (1) | US10300050B2 (ru) |
EP (2) | EP4265298A3 (ru) |
JP (3) | JP6820344B2 (ru) |
KR (2) | KR20180121900A (ru) |
CN (1) | CN108883101A (ru) |
AU (2) | AU2017215300B2 (ru) |
CA (1) | CA3013454C (ru) |
DK (1) | DK3411029T3 (ru) |
ES (1) | ES2963451T3 (ru) |
GB (2) | GB201602145D0 (ru) |
MX (1) | MX2018009364A (ru) |
PL (1) | PL3411029T3 (ru) |
PT (1) | PT3411029T (ru) |
SI (1) | SI3411029T1 (ru) |
WO (1) | WO2017134468A1 (ru) |
ZA (1) | ZA201805296B (ru) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019020993A1 (en) | 2017-07-24 | 2019-01-31 | Achieve Pharma Uk Limited | CYTISINE SALTS |
EP3598968A1 (en) * | 2018-07-23 | 2020-01-29 | Adamed Pharma S.A. | Solid pharmaceutical cytisine composition |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB201602145D0 (en) * | 2016-02-05 | 2016-03-23 | Achieve Pharma Uk Ltd | Salt |
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EP1586320A1 (en) * | 2004-04-16 | 2005-10-19 | Sopharma AD | Cytisine containing solid dosage form |
WO2014076680A1 (en) * | 2012-11-19 | 2014-05-22 | Aflofarm Farmacja Polska Spolka Z Ograniczona Odpowiedzialnoscia | Solid dosage form comprising micronized cytisine |
EP2957280A1 (en) * | 2014-06-18 | 2015-12-23 | Pharmacia Polonica Spolka z Ograniczona Odpowiedzialnoscia | Solid pharmaceutical composition of cytisine and process for preparation thereof |
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GB201602145D0 (en) * | 2016-02-05 | 2016-03-23 | Achieve Pharma Uk Ltd | Salt |
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2016
- 2016-02-05 GB GBGB1602145.3A patent/GB201602145D0/en not_active Ceased
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2017
- 2017-02-06 CN CN201780009979.0A patent/CN108883101A/zh active Pending
- 2017-02-06 MX MX2018009364A patent/MX2018009364A/es active IP Right Grant
- 2017-02-06 PT PT177048147T patent/PT3411029T/pt unknown
- 2017-02-06 PL PL17704814.7T patent/PL3411029T3/pl unknown
- 2017-02-06 KR KR1020187025475A patent/KR20180121900A/ko not_active Application Discontinuation
- 2017-02-06 DK DK17704814.7T patent/DK3411029T3/da active
- 2017-02-06 US US16/075,902 patent/US10300050B2/en active Active
- 2017-02-06 EP EP23197173.0A patent/EP4265298A3/en active Pending
- 2017-02-06 SI SI201731450T patent/SI3411029T1/sl unknown
- 2017-02-06 JP JP2018541196A patent/JP6820344B2/ja active Active
- 2017-02-06 KR KR1020247009722A patent/KR20240042257A/ko active Search and Examination
- 2017-02-06 WO PCT/GB2017/050294 patent/WO2017134468A1/en active Application Filing
- 2017-02-06 AU AU2017215300A patent/AU2017215300B2/en active Active
- 2017-02-06 ES ES17704814T patent/ES2963451T3/es active Active
- 2017-02-06 EP EP17704814.7A patent/EP3411029B1/en active Active
- 2017-02-06 CA CA3013454A patent/CA3013454C/en active Active
- 2017-02-06 GB GB1701939.9A patent/GB2550241B/en active Active
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2018
- 2018-08-10 ZA ZA2018/05296A patent/ZA201805296B/en unknown
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2021
- 2021-01-04 JP JP2021000114A patent/JP7292316B2/ja active Active
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2022
- 2022-06-02 AU AU2022203808A patent/AU2022203808B2/en active Active
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2023
- 2023-06-06 JP JP2023092903A patent/JP2023113803A/ja active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1586320A1 (en) * | 2004-04-16 | 2005-10-19 | Sopharma AD | Cytisine containing solid dosage form |
WO2014076680A1 (en) * | 2012-11-19 | 2014-05-22 | Aflofarm Farmacja Polska Spolka Z Ograniczona Odpowiedzialnoscia | Solid dosage form comprising micronized cytisine |
EP2957280A1 (en) * | 2014-06-18 | 2015-12-23 | Pharmacia Polonica Spolka z Ograniczona Odpowiedzialnoscia | Solid pharmaceutical composition of cytisine and process for preparation thereof |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2019020993A1 (en) | 2017-07-24 | 2019-01-31 | Achieve Pharma Uk Limited | CYTISINE SALTS |
US11459328B2 (en) | 2017-07-24 | 2022-10-04 | Achieve Pharma Uk Limited | Cytisine salts |
EP3598968A1 (en) * | 2018-07-23 | 2020-01-29 | Adamed Pharma S.A. | Solid pharmaceutical cytisine composition |
WO2020020711A3 (en) * | 2018-07-23 | 2020-06-11 | Adamed Pharma S.A. | Solid pharmaceutical cytisine composition |
Also Published As
Publication number | Publication date |
---|---|
AU2022203808A1 (en) | 2022-06-23 |
CN108883101A (zh) | 2018-11-23 |
CA3013454C (en) | 2020-02-25 |
GB201602145D0 (en) | 2016-03-23 |
MX2018009364A (es) | 2019-05-15 |
DK3411029T3 (da) | 2023-11-27 |
AU2022203808B2 (en) | 2023-10-19 |
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EP3411029B1 (en) | 2023-11-01 |
JP7292316B2 (ja) | 2023-06-16 |
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PL3411029T3 (pl) | 2024-01-29 |
GB2550241B (en) | 2018-04-25 |
SI3411029T1 (sl) | 2024-04-30 |
JP6820344B2 (ja) | 2021-01-27 |
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AU2017215300A1 (en) | 2018-08-23 |
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ES2963451T3 (es) | 2024-03-27 |
JP2021073197A (ja) | 2021-05-13 |
KR20240042257A (ko) | 2024-04-01 |
CA3013454A1 (en) | 2017-08-10 |
JP2019504848A (ja) | 2019-02-21 |
ZA201805296B (en) | 2019-04-24 |
US10300050B2 (en) | 2019-05-28 |
GB2550241A (en) | 2017-11-15 |
EP3411029A1 (en) | 2018-12-12 |
AU2017215300B2 (en) | 2022-03-03 |
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US20190038608A1 (en) | 2019-02-07 |
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